I also pushed really hard to buy my first property this past summer, a student-rental that I would house hack in as I'm a sophomore in college.

If the mechanicals of the home (plumbing, electrical, roof, and HVAC) are all centralized to a single unit, I think your home inspector stands a much better chance of spotting an issue as opposed to a multi-unit with multiple independent systems that may or may not be accessible due to tenants.As for closing costs, try to push the closing date until you have the funds available?

I am also very introverted and have been pushing myself way outside my comfort zone the past couple months networking and interacting with investors/property managers/realtors. 

If you make the offer, be ready for a desperate seller to accept and follow through.

Follow the local expectations of the tenants that you are attracting, spreading the improvements as the budget allows. 

I've found that sometimes just having an attorney reach out can open up a conversation again, and it might save you the grief and time of having to push through to foreclosure.

It looks like the verdict is unanimous:  I'm not going to try to push anything.

And each strategy is going to be based off of the amount of risk you're willing to endure, just like any investment, and your return will follow. 

The 1031 exchange is a sale of investment real estate followed by a purchase of investment real estate. 

As a result, I never get push back on the contract and people will sign literally at the kitchen table without reading in detail.